For academics and activists interested in the possibility of moving away from the extractivist, capitalistic, and consolidated agricultural systems supported by the present global food regime, Cuba is a fascinating case. Since the onslaught of the Special Period and the economic scarcity that it produced, the Cuban state has arguably offered more political, infrastructural, and ideological support for local, diversified, and agroecological farming than any other. And yet, many farmers, technicians, administrators, political leaders, and everyday citizens continue to support and/or practice models of conventional agriculture, leading observers to wonder if agricultural transition will be reversed as the Special Period recedes into the past. This dissertation, based on fieldwork conducted between 2011 and 2016, argues that the Cuban alternative agriculture movement cannot be understood merely as a reaction to the economic scarcity provoked by the Special Period. It describes the emergence of sustainable agriculture movements in one central province, revealing how promotion by non-state entities increased even after the Special Period was over. The dissertation identifies the permaculture network of the Antonio Nuñéz Jiménez Foundation for Nature and Man (FANJ) as the most active source of alternative agriculture promotion in the province during the research period, and argues that by creating and reproducing a “figured world” of permaculture through situated communities of practice, FANJ has supported subjective shifts, which have further committed participants to sustainability-oriented practices. It describes these participants as motivated by an entangled set of material and moral motivations, including a desire to escape a sentiment of frustration and disillusionment. Thus, the dissertation depicts Cuban alternative agriculture as a set of enduring movements that are supported by non-state individuals and organizations. It underscores the importance of collective meaning, learning, and subjectivity in processes of agricultural transformation, and suggests that organizations able to form local communities of practice are well positioned to encourage alternative agriculture practices.